Oscar Style Dos and Don’ts

Oscar Style Dos and Don’ts

Sequins and feathers and beads—oh my! Here’s a look at the prettiest, boldest and most disastrous creations ever to show up on the red carpet at the Academy Awards.

Tinseltowners, DO take the opportunity to bring out—OK, borrow—some multicarat, million-dollar-plus jewels. It gives us something pretty to look at while the winners of the more obscure awards, like Best Caterer in Cold Weather, drone on and thank their moms and childhood pets.

Just DON’T wear those gems on your feet. Paul Simon’s “Diamonds on the Soles of Her Shoes” lyrics are rad and all, but $2 million, multicarat heels just seem silly, not to mention an insurance nightmare.

A black gown on the most photographed, highly anticipated (and critiqued) red carpet in the world? Snooze. But an ill-fitting black gown on the Oscar red carpet? A definite DON’T (and a good reason to think about finding a new stylist).

Wearing an unexpected color totally works. At the 2008 Oscars, Jennifer Hudson stood out from the sea of black tuxes and dark ball gowns by wearing a white Roberto Cavalli gown. Of course, her gorgeous smile and A-list status didn’t hurt either.

Sure, garbage bag-like designer gowns may seem dramatic on the runway, but in person it’s just, how should we put this, a major DON’T. Back-scratching poses should also be skipped.

Madonna was Michael Jackson’s date to the 1990 Oscars. No skimping on sequins here!

Photo: Joyce Silverstein/Rex USA

Gwyneth Paltrow was pretty in pink Ralph Lauren, but her dress was kinda saggy in the front. Hint: Before you step in front of the cameras, make sure that top fits!

Photo: Rex USA

Through the years, Cher has shown up at the Oscars in one jaw-dropping ensemble after another: Here, a 1986 number by Bob Mackie. In Glamour’s book, she’s always a “Do”—for entertainment value alone!

Photo: Corbis

The year she picked up the first-ever Best Actress Oscar awarded to an African-American woman (for 2001’s Monster’s Ball), Halle Berry shined in beaded Elie Saab.

Photo: Steve Granitz/WireImage.com

The other taller-than-Tom beauty he escorted down the red carpet: Nicole Kidman became an A-list style star in an Asian-inspired John Galliano for Christian Dior gown in 1997.

Photo: Kevin Mazur/WireImage.com

They were cute: Hilary Swank, who wore gold Randolph Duke and took home gold for her role in 1999’s Boys Don’t Cry, walked the red carpet with Chad Lowe. (Yep, that was the year she forgot to thank him!)

Photo: Jeff Vespa/WireImage.com

Then-super couple Ellen DeGeneres and Anne Heche in 1999: a bold style statement in a white tux and gown.

Photo: Andrew Shawaf/Getty Images

Catherine Zeta-Jones thrilled the tough-to-please fashion crowd in 1999 in a stunning red strapless number by Versace. It was her first time at the Oscars, too: Impressive!

Photo: Rex USA

On the arm of her dad, Uma Thurman debuted the lavender Prada dress that launched a thousand “Best Dressed” nods in 1995.

Maybe Jodie Foster never got to attend her eighth grade prom, or maybe she just wanted to match the curtains backstage. Either way, her dress choice for the 61st Annual Academy Awards in 1989—not so good.

Photo: Ron Galella/WireImage.com

At the 1995 Oscars, Courtney Love and then-It girl Amanda de Cadenet proved that while matching outfits will get you attention, they won’t guarantee good taste.

Photo: Rex USA

Barbra Streisand left little to the imagination when she wore this see-through, beaded creation to the 1969 Awards—and showed no sign of her legendary stage fright.

Photo: Corbis

Move over, Cher! The swan dress Björk wore to the 73rd Annual Academy Awards in 2001, designed by her close friend Marjan Pejoski, landed her in the all-time hall of fame for fabulous Don’ts.

Photo: Steve Granitz/WireImage.com

Celine Dion turned her tux around in 1999 at the 71st Annual Academy Awards…and turned every fashion critic against her.

Photo: Jim Smeal/WireImage.com

Yep, it’s Demi Moore in 1989 at the 61st Annual Academy Awards wearing, umm, biker shorts, a brocade train and matching bra. Insane, yes, but Ashton still fell in love with her 14 years later.